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Bromoeterificación asimétrica catalítica y desimetrización de 1,3-diolos olefínicos con sulfuros simétricos C2 y sus
Zhihai Ke1, Chong Kiat Tan, Feng Chen
1Department of Chemistry, National University of Singapore , 3 Science Drive 3, Singapore 117543.
Journal of the American Chemical Society
|April 5, 2014
Resumen
Un nuevo catalizador de sulfuro cíclico permite la bromoeterificación enantioselectiva y la desimetrización de los diolos. Este método es clave para sintetizar el fármaco antifúngico posaconazol (Noxafil).
Área de la Ciencia:
- Química orgánica es la química orgánica.
- La catálisis es la catálisis.
- Química Medicinal La Química Medicinal es el campo de la Química Medicinal.
Sus antecedentes:
- Los 1,3-diolos olefínicos son precursores sintéticos muy versátiles.
- El desarrollo de reacciones enantioselectivas y diastereoselectivas es crucial en la síntesis de fármacos.
- El posaconazol (Noxafil) es un importante medicamento antifúngico activo por vía oral.
Objetivo del estudio:
- Desarrollar un nuevo método catalítico para la bromoeterificación y desimetrización enantioselectiva y diastereoselectiva de 1,3-diolos olefínicos.
- Para aplicar esta metodología a la síntesis de un intermediario clave para el posaconazol.
Principales métodos:
- Utilizó un catalizador de sulfuro cíclico C2-simétrico.
- Se realizó una bromoeterificación enantioselectiva.
- Se logró la desimetrización diastereoselectiva de los 1,3-diolos olefínicos.
Principales resultados:
- Desarrolló un protocolo de bromoeterificación y desimetrización altamente enantioselectivo y diastereoselectivo.
- Se sintetizó con éxito un intermediario clave para el posaconazol utilizando el método desarrollado.
Conclusiones:
- El sistema catalítico desarrollado proporciona una ruta eficiente para la síntesis de moléculas complejas.
- Esta metodología es valiosa para la preparación de agentes antifúngicos como el posaconazol.
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